As the offspring of producer/writer Naomi Foner and director Stephen Gyllenhaal, it is not surprising that Jake Gyllenhaal has been acting since childhood. Raised in Los Angeles, Gyllenhaal acted in school plays and made his winsome screen debut when he was in the fifth grade, playing Billy Crystal's son in the blockbuster summer comedy City Slickers (1991). Keeping it in the family while acting with some of the industry's most notable talents, Gyllenhaal subsequently appeared in his parents' 1993 adaptation of the novel A Dangerous Woman with Debra Winger, and played Robin Williams' son in a 1994 episode of TV's Homicide that was directed by his father.
Poised to make the transition from child to adult actor, Gyllenhaal earned rave reviews, heralding him as a star in the making, for his emotionally sincere performance as real-life rocket builder Homer Hickam in the warmly received drama October Sky (1999). Though he opted to stay in school and attend college at Columbia University, Gyllenhaal continued his creative pursuits, playing in a rock band and starring as the oddball title character alongside Drew Barrymore in the Barrymore-produced Sundance Film Festival entrant Donnie Darko (2001). Gyllenhaal could be seen later that same year as the titular character in the ill-fated Bubble Boy.